First Total Syntheses of Tetracenomycins C and X | Zendy

Sato Shogo | Zendy; Sakata Keiichiro | Zendy; Hashimoto Yoshimitsu | Zendy; Takikawa Hiroshi | Zendy; Suzuki Keisuke | Zendy

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First Total Syntheses of Tetracenomycins C and X

Author(s) -

Sato Shogo,

Sakata Keiichiro,

Hashimoto Yoshimitsu,

Takikawa Hiroshi,

Suzuki Keisuke

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201707099

Subject(s) - stereocenter , aryne , isoxazole , chemistry , benzoin , ring (chemistry) , stereoselectivity , acetal , total synthesis , stereochemistry , oxide , medicinal chemistry , enantioselective synthesis , organic chemistry , catalysis

The first total syntheses of tetracenomycins C and X were achieved, featuring 1) preparation of a hexasubstituted naphthonitrile oxide by successive benzyne cycloadditions and an oxidative ring‐opening reaction; 2) a novel ortho ‐quinone mono‐acetal as the A‐ring unit; 3) construction of three contiguous stereogenic centers by an asymmetric benzoin cyclization, an isoxazole oxidation, and a stereoselective reduction.

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